Reaktion #7831

Reaktionsgleichung

Thionyl chloride

3,5-dimethoxy-4-methylbenzoic acid

2-aminophenol

diisopropylethyl amine

→

3,5-dimethoxy-N-(2-methoxyphenyl)-4-methylbenzamide

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Sonstigereaction mixture to rt
3. 3
   Einengenconcentrated mixture in vacuo
4. 4
   EinengenAfter concentrating mixture in vacuo
5. 5
   Sonstigethe resulting brown oil was purified by flash chromatography on silica gel
6. 6
   Waschena gradient elution from 1:9 EtOAc

Vorschrift

Thionyl chloride (10 mL) and 3,5-dimethoxy-4-methylbenzoic acid (1.0 g, 5.1 mmol) was refluxed under argon until no starting material was observed by TLC. After cooling reaction mixture to rt, concentrated mixture in vacuo. The resulting brown oil was added to a mixture of 2-aminophenol (580 mg, 5.3 mmol), diisopropylethyl amine (1.1 mL, 6.3 mmol) and THF (40 mL) at 0° C. and then brought to rt overnight. After concentrating mixture in vacuo, the resulting brown oil was purified by flash chromatography on silica gel, using a gradient elution from 1:9 EtOAc:hexanes to 1:1 EtOAc:hexanes. This afforded the desired intermediate, 3,5-dimethoxy-N-(2-methoxyphenyl)-4-methylbenzamide, as a colorless solid.

Quelle